


All Day

by KillerOfHope



Series: All & Everything [1]
Category: Supernatural
Genre: Alternate Universe - Always a Different Sex, Bottom Dean, F/M, Genderbending, M/M, Pegging, Strap-Ons
Language: English
Status: Completed
Published: 2015-07-15
Updated: 2015-07-15
Packaged: 2018-04-09 12:00:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,025
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4347929
Author URL: https://archiveofourown.org/users/KillerOfHope/pseuds/KillerOfHope
Summary: <blockquote class="userstuff">
              <p>Samantha makes Dean drop his pants whenever she wants. Yet her brother never protests.</p>
            </blockquote>





	All Day

Dean swallowed at the harness his sister is wearing. Not even her blazing smile can distract him from the sight of the black toy attached to Sam's crotch. Otherwise his sister is just dressed in one of her usual shirts, buttons open and barely hiding her huge breasts. Dean loves to play with them, sucking, touching, kneading them ... if Sam permits it. 

Right now she's stroking her fake cock and Dean knows he won't get what he wants unless ... 

"Fuck Sam," he curses and walks over to his sister, going on his knees as if it was natural. He opens his mouth to suck Sam's cock but she stops him by fisting his hair, pulling him back. 

"Uh hn, dear brother," she tells him with a smile. "Nothing of that. I just want to fuck you so if would please turn around?"

Dean can't even fucking protested when she ask him so sweetly and manhandles him into the right position. Pulling Dean's jeans down is an easy job and quickly her fingers find the hole hidden in the cleft of her brother's ass. She notices how his breathing quickens when opens the cap of the lube. It's a familiar sound for her brother. 

Reaching between his parted legs Sam finds the cock already half-hard, waiting for attention. 

"Can't wait, can you?" Sam says and starts to rub her slick fingers against his entrance. "You're always so fucking eager to get pegged by your sister, hn?"

When Sam gets no response, she slaps his ass once as a reminder. 

"God. Yeah, I like it," Dean breathes, thinking of all the other times. The most recent one was just yesterday evening. In the kitchen where she had him bend over the table. 

Smiling Sam runs her thumb over the ring of muscles. It's pink and twitching in anticipation. She's more familiar with his than her own. 

"You could help me out a bit," Sam hums. "I can barely see your tight little hole. Why don't you spread you ass a bit?"

With a moan Dean reaches behind him to pull his cheeks apart for Sam. It doesn't matter for him that his face rests on the floor now since his sister makes a noise of approval and the first finger slips in. Despite his efforts his breathing hitches slightly. He might be used to it but it goes in so easily, Sam starts fucking him with her fingers. In and out. Always in and out. Dean barely takes notices of the second fingers. 

His flesh yields so easily for his sister, it frightens him sometimes. 

"Sam?" he asks when his hands are taken from his ass. It's Sam's now. Again. Free to use it as she pleases. 

When Dean feels her running the palms of her hands over his bottom and his lower back, he knows what comes next. Sam doesn't even have to nudge his thighs apart, Dean does it all on his own when she finally takes his hips into her hands and guides her cock to his entrance. 

"Hnng." A small sound leaves Dean's mouth when the head of the black toy starts to push into him. No matter how much lube she uses, his sister's cock always makes him feel overwhelmed. Dean braces him onto his elbows and lets Sam draw his body back with her strength alone. Leaves it up to her to lower him on her cock until it's buried inside. 

"Easy," she murmurs and strokes Dean's cock. 

He's thankful for it, the strap-on robs him all of his breath as he lies on the floor with his ass high in the air. It's impaling him, so huge and wide in his ass. It feels like as if the strap-on is slitting him apart and yet Dean can't imagine his sex life without it. Sam never makes him take more than he's able to. 

And like always she starts moving just as he wants to tell her it's okay. 

"Oh. Oooh...," Dean moans and closes his eyes. The motions are slow and even, yet his whole body responds to Sam's movements. She still owns his hips with her gentle grip and Dean rocks back onto the toy. Not much. He's using little tiny waves to have the toy never leave him, clenching his ass around until he hears the squelching sound of sweaty flesh meeting plastic. 

"You're doing well, Dean," Sam tells him, guiding his hips only a little. "It's such a good position for you. I barely have to do anything." 

With a silent shout Dean's sweaty forehead touches the carpet as his sister praises continue, her large frame looming compared to him. His movements get more erratic with each time the cock drags in and out of him. The pace isn't fast nor hard and punishing but Dean is on the bring of his orgasm. But the strap-on sets him on fire this evening. 

Dean nearly screams when Sam touches his cock. His body shudders when he finally comes while Sam keeps him impaled on the strap-on with her hands. She pets his hair after as he's laying on the carpet riding out the aftershocks, still half-dressed while he sees Sam's long legs somewhere next to him. 

"Did you get off?" he mumbles tired and worn out. Dean hopes because his sister is a beast and there's no hope of getting up right now. 

"I get off on seeing you like this." Dean turns his head to meet her gaze, she smiles wickedly. "Besides I still have this," she says and strokes the black strap-on she's still wearing. 

Dean's heart stutters a little bit when he realizes Sam has no intention of taking it off anytime soon. So he watches her disappear into the kitchen, fetching him a glass of water while the strap-on still stands proudly between her legs. With a groan Dean turns around until he's laying on his back at least. Sam'll be back soon and she isn't done with him yet. 

But there's no use in lying to himself. He could stay here all day and take her thrusts and not get tired of it.

**Author's Note:**

> I always wanted to write girl!Sam with bottom!Dean. Here it is.


End file.
